Discovery of indole-based tetraarylimidazoles as potent inhibitors of urease with low antilipoxygenase activity

Eur J Med Chem. 2015 Sep 18:102:464-70. doi: 10.1016/j.ejmech.2015.08.011. Epub 2015 Aug 13.

Abstract

A series of tetraarylimidazoles (5A-5O) were prepared by one pot four component condensation reactions of 2-arylindole-3-carbaldehydes, substituted anilines, benzil and ammonium acetate in acetic acid. The synthesized compounds exhibited potent antiurease activity with IC50 values ranging from 0.12 ± 0.06 μM to 29.12 ± 0.18 μM as compared with thiourea. However, low inhibition profiles were observed for lipoxygenase. The data show that tetraarylimidazoles containing a substituted 2-penylindole have emerged as a new class of potent inhibitors of urease enzyme.

Keywords: Ammonium acetate; Lipoxygenase inhibition; Multicomponent reaction; Thiourea; Urease inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Canavalia / enzymology
  • Dose-Response Relationship, Drug
  • Drug Discovery*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Imidazoles / chemical synthesis
  • Imidazoles / chemistry
  • Imidazoles / pharmacology*
  • Lipoxygenase / metabolism*
  • Molecular Structure
  • Structure-Activity Relationship
  • Urease / antagonists & inhibitors*
  • Urease / metabolism

Substances

  • Enzyme Inhibitors
  • Imidazoles
  • Lipoxygenase
  • Urease